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WO2013100540A1 - Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le contenant, et dispositif d'affichage contenant ledit dispositif électroluminescent organique - Google Patents

Composé pour dispositif optoélectronique organique, dispositif électroluminescent organique le contenant, et dispositif d'affichage contenant ledit dispositif électroluminescent organique Download PDF

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WO2013100540A1
WO2013100540A1 PCT/KR2012/011433 KR2012011433W WO2013100540A1 WO 2013100540 A1 WO2013100540 A1 WO 2013100540A1 KR 2012011433 W KR2012011433 W KR 2012011433W WO 2013100540 A1 WO2013100540 A1 WO 2013100540A1
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이호재
김형선
민수현
박무진
유은선
채미영
천태규
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Cheil Industries Inc
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Definitions

  • the present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having excellent life, efficiency, electrochemical stability, and thermal stability, an organic light emitting device including the same, and a display device including the organic light emitting device.
  • An organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.
  • Organic optoelectronic devices can be divided into two types according to the operation principle.
  • excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.
  • the second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are used to inject or transport holes or electrons to drive the device. Injection or transport materials, or luminescent materials.
  • organic light emitting diodes are attracting attention as the demand for flat panel displays increases.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
  • the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.
  • the host / dopant system can be used as a light emitting material.
  • materials constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • a hole injection material such as a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • This stable and efficient material should be preceded, and development of a stable and efficient organic material layer for an organic light emitting device has not been made yet, and therefore, development of new materials is continuously required.
  • the necessity of such a material development is the same in the other organic optoelectronic devices described above.
  • the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum evaporation method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode using the inkjet or spin coating method has low initial investment cost. Large area has an advantage.
  • Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
  • advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
  • LCD liquid crystal display
  • the luminous efficiency In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. In this case, the light emitting efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting layer.
  • the electron mobility of the organic material is generally slower than the hole mobility, in order to efficiently combine holes and electrons in the light emitting layer, an efficient electron transport layer is used to increase the electron injection and mobility from the cathode, It should be able to block the movement of holes.
  • a compound for an organic optoelectronic device which can play a role of hole injection and transport or electron injection and transport, and can act as a light emitting host with an appropriate dopant.
  • An organic light emitting diode having excellent lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability and a display device including the same are provided.
  • a compound for an organic optoelectronic device represented by the following Chemical Formula 1 is provided.
  • L is any one of the following Formulas 2 to 4, L 2 and L 3 are independently a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynyl Ethylene group, substituted or unsubstituted C6 to C30 arylene group or substituted or unsubstituted C2 to C30 heteroarylene group, Ar 2 and Ar 3 is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted A C6 to C36 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties , n2 and n3 are any integers from 0 to 3, m2 and m3 are 1:
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group.
  • L 1 is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to A C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group
  • n1 is an integer of any one of 0 to 3
  • Ar 1 is hydrogen, deuterium, substituted or Unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C
  • the compound for an organic optoelectronic device may be represented by the following formula (5).
  • L 2 and L 3 are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group Or a substituted or unsubstituted C2 to C30 heteroarylene group
  • Ar 2 and Ar 3 are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties
  • n2 and n3 are any of integers from 0 to 3
  • the compound for an organic optoelectronic device may be represented by the following formula (6).
  • L 2 and L 3 are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group Or a substituted or unsubstituted C2 to C30 heteroarylene group
  • Ar 2 and Ar 3 are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties
  • n2 and n3 are any of integers from 0 to 3
  • the compound for an organic optoelectronic device may be represented by the following formula (7).
  • L 2 and L 3 are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group Or a substituted or unsubstituted C2 to C30 heteroarylene group
  • Ar 2 and Ar 3 are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties
  • n2 and n3 are any of integers from 0 to 3
  • M1 and n1 may be 0.
  • Ar 2 and Ar 3 may be a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties.
  • Substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties is substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted carba Zolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted or unsubstituted thiazazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted Benzotriazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsub
  • the substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be represented by any one of the following Chemical Formulas 8 to 12.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-48.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-48.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas C-1 to C-48.
  • the compound for an organic optoelectronic device may be a triplet excitation energy (T1) 2.0 eV or more.
  • the organic optoelectronic device may be selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode
  • at least one of the organic thin film layer is the above-described organic optoelectronic device It provides an organic light emitting device comprising a compound for.
  • the organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
  • the compound for an organic optoelectronic device may be included in a hole transport layer or a hole injection layer.
  • the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material in the light emitting layer.
  • a display device including the organic light emitting diode described above is provided.
  • Such a compound can be used as a hole injection / transport material, a host material, or an electron injection / transport material for the light emitting layer.
  • the organic optoelectronic device using the same has excellent electrochemical and thermal stability, and has excellent life characteristics, and may have high luminous efficiency even at a low driving voltage.
  • 1 to 5 are cross-sectional views illustrating various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • hole injection layer 230 light emitting layer + electron transport layer
  • substituted means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C1 to C10 such as C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc. Mean substituted by a trifluoroalkyl group or a cyano group.
  • substituted halogen, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to Two adjacent substituents of C1 to C10 trifluoroalkyl group or cyano group such as C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group and trifluoromethyl group may be fused to form a ring. .
  • hetero means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon.
  • an "alkyl group” means an aliphatic hydrocarbon group.
  • the alkyl group may be a "saturated alkyl group” that does not contain any double or triple bonds.
  • Alkenylene group means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond
  • alkynylene group means at least two carbon atoms of at least one carbon-carbon triplet. It means a functional group consisting of a bond.
  • the alkyl group, whether saturated or unsaturated, may be branched, straight chain or cyclic.
  • the alkyl group may be an alkyl group that is C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • the alkyl group is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohex It means a practical skill.
  • Aromatic group means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.
  • Heteroaryl group means containing 1 to 3 hetero atoms selected from the group consisting of N, O, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
  • the carbazole derivative refers to a structure in which a nitrogen atom of a substituted or unsubstituted carbazolyl group is substituted with a hetero atom instead of nitrogen.
  • Specific examples thereof include dibenzofuran (dibenzofuranyl group) and dibenzothiophene (dibenzothiophenyl group).
  • the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate the injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer.
  • an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer.
  • Compound for an organic optoelectronic device includes a core comprising a carbazolyl group and at least one phenylenyl group bonded to the carbazolyl group and a substituent having at least one electronic property bonded to the phenylenyl group. can do.
  • the substituent having at least one electronic property bonded to the phenylenyl group may be a meta position.
  • the substituent is a meta position
  • the conjugation from the core including the carbazolyl group and the at least one phenylene group bonded to the carbazolyl group to the substituent having electronic properties is broken at the metasubstituent position.
  • the solubility of the compound is relatively improved as compared to the case connected to the para position, which has the advantage of facilitating material synthesis.
  • the carbazolyl group of the core may optionally include a substituent having hole characteristics.
  • the HOMO and LUMO levels of the entire compound can be appropriately adjusted as necessary, thereby preparing a compound for an organic optoelectronic device having various energy levels.
  • the core structure may be used as a light emitting material, a hole injection material or a hole transport material of an organic optoelectronic device because it includes a substituent having an electronic property of carbazolyl group having excellent hole properties. In particular, it may be suitable for the light emitting material.
  • the substituent having at least one electronic property bonded to the phenyl group of the core may be a meta position, the symmetry in the entire molecule may be reduced, and thus the crystallinity of the compound may be lowered, and thus recrystallization is suppressed in the device.
  • At least one of the substituents bonded to the core may be a substituent having electronic properties. Therefore, the compound may satisfy the conditions required in the light emitting layer by reinforcing the electronic properties in the carbazole structure having excellent hole properties. More specifically, it can be used as a host material of the light emitting layer.
  • the compound for an organic optoelectronic device may be a compound having various energy band gaps by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.
  • the hole transport ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in organic chemical and thermal stability It is possible to improve the life characteristics when driving the device.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device represented by the formula (1).
  • L is any one of the following Formulas 2 to 4, L 2 and L 3 are independently a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynyl Ethylene group, substituted or unsubstituted C6 to C30 arylene group or substituted or unsubstituted C2 to C30 heteroarylene group, Ar 2 and Ar 3 is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted A C6 to C36 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties , n2 and n3 are any integers from 0 to 3, m2 and m3 are 1:
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group.
  • L 1 is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to A C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group
  • n1 is an integer of any one of 0 to 3
  • Ar 1 is hydrogen, deuterium, substituted or Unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C
  • the compound for an organic optoelectronic device may be a substituted or unsubstituted C2 to C30 heteroaryl group having at least one of Ar 2 and Ar 3 , and the compound for an organic optoelectronic device may emit light, holes or Electronic properties; Membrane stability; Thermal stability and high triplet excitation energy (T1).
  • the two substituents bonded to the phenylenyl group present in Formulas 2 to 4 may be a meta position.
  • a substituent exists in the meta position, a structure having an asymmetric bipolar characteristic can be manufactured, and the structure of the asymmetric bipolar characteristic can be expected to improve light emitting efficiency and performance of the device by improving hole and electron transfer capability.
  • the structure of the compound can be prepared in bulk by the control of the substituent, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be longer.
  • the compound for an organic optoelectronic device may be represented by Formula 5 more specifically.
  • L 2 and L 3 are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group Or a substituted or unsubstituted C2 to C30 heteroarylene group
  • Ar 2 and Ar 3 are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties
  • n2 and n3 are any of integers from 0 to 3
  • the compound for an organic optoelectronic device may be represented by Formula 6 more specifically.
  • L 2 and L 3 are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group Or a substituted or unsubstituted C2 to C30 heteroarylene group
  • Ar 2 and Ar 3 are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties
  • n2 and n3 are any of integers from 0 to 3
  • the compound for an organic optoelectronic device may be represented by the following formula (7).
  • L 2 and L 3 are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group Or a substituted or unsubstituted C2 to C30 heteroarylene group
  • Ar 2 and Ar 3 are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar 2 and Ar 3 is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties
  • n2 and n3 are any of integers from 0 to 3
  • L 1 to L 3 are substituted or unsubstituted phenylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted terphenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted Anthracenylene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted fluorenylene group and the like.
  • M1 and n1 may be 0.
  • Ar 2 and Ar 3 may be a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties.
  • the substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties is substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted Substituted carbazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted or unsubstituted cythiazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted A substituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted
  • substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be a substituent represented by any one of the following Formulas 8 to 12.
  • Ar 1 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substituted or unsubstituted C2 to C30 heteroaryl group having a hole property, a substitution Or an unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group.
  • the substituted or unsubstituted C6 to C30 aryl group having the above hole properties is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted anthracenyl group , Substituted or unsubstituted fluorenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted spiro-fluorenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted pyrenyl group, substituted or It may be an unsubstituted perenyl group or a combination thereof.
  • substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics is substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted Ring indol carbazolyl group;
  • the aryl group or heteroaryl group which is a substituent bonded to the nitrogen of the substituted or unsubstituted arylamine group and substituted or unsubstituted heteroarylamine group is more specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group , Substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or un
  • the compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-48.
  • the compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-48.
  • the compound for an organic optoelectronic device may be represented by any one of Formulas C-1 to C-48.
  • introducing a functional group having the electronic characteristics is effective for improving the lifespan and driving voltage of the organic light emitting diode.
  • nonlinear optical material since the compound for an organic optoelectronic device has photoactive and electrical activity, nonlinear optical material, electrode material, color change material, optical switch, sensor, module, wave guide, organic transistor, laser, light absorber, dielectric and separator It can also be very usefully applied to materials such as (membrane).
  • the compound for an organic optoelectronic device including the compound as described above has a glass transition temperature of 90 ° C. or higher, and a thermal decomposition temperature of 400 ° C. or higher, thereby providing excellent thermal stability. This makes it possible to implement a high efficiency organic photoelectric device.
  • the compound for an organic optoelectronic device including the compound as described above may serve as light emission, electron injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic optoelectronic device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, or an electron transport material.
  • Compound for an organic optoelectronic device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
  • one embodiment of the present invention provides an organic optoelectronic device comprising the compound for an organic optoelectronic device.
  • the organic optoelectronic device refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, and the like.
  • a compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, a gate, a source-drain electrode, or the like may be used as an electrode material. Can be used.
  • Another embodiment of the present invention is an organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least any one of the organic thin film layer is an embodiment of the present invention It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to.
  • the organic thin film layer which may include the compound for an organic optoelectronic device may include a layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof. At least one of the layers includes the compound for an organic optoelectronic device according to the present invention.
  • the hole transport layer or the hole injection layer may include a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the compound for an organic optoelectronic device when included in a light emitting layer, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.
  • FIG. 1 to 5 are cross-sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the organic light emitting diodes 100, 200, 300, 400, and 500 according to the embodiment of the present invention are interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.
  • the anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly injected into the organic thin film layer.
  • the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO 2 and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • the negative electrode 110 includes a negative electrode material, and the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al.
  • Multilayer structure materials such as LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
  • a metal electrode such as aluminum may be used as the cathode.
  • FIG. 1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105.
  • the organic thin film layer 105 may exist only as a light emitting layer 130.
  • FIG. 2 illustrates a two-layered organic light emitting diode 200 including an emission layer 230 and an hole transport layer 140 including an electron transport layer as the organic thin film layer 105, as shown in FIG. 2.
  • the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140.
  • the light emitting layer 130 functions as an electron transporting layer
  • the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ITO.
  • FIG. 3 is a three-layered organic light emitting device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, and the organic thin film layer 105.
  • the light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.
  • FIG. 4 illustrates a four-layered organic light emitting diode 400 in which an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 exist as an organic thin film layer 105.
  • the hole injection layer 170 may improve adhesion to ITO used as an anode.
  • the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105 and their Any one selected from the group consisting of a combination includes the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and the hole blocking layer (not shown) is included in the electron transport layer. It is desirable to provide an organic light emitting device having a simplified structure because it does not need to be formed separately.
  • the compound for an organic optoelectronic device when included in the light emitting layers 130 and 230, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.
  • the above-described organic light emitting device includes a dry film method such as an evaporation, sputtering, plasma plating and ion plating after forming an anode on a substrate;
  • the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
  • a display device including the organic light emitting diode is provided.
  • reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 57 g (71% yield) of the compound (L).
  • reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 35 g (66% yield) of compound (M).
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol and the like
  • HTM vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 1200 ⁇ .
  • Example 1 The material synthesized in Example 1 was used as a host on the hole transport layer, and a phosphorescent green dopant was doped with PhGD (see the following formula) at 7 wt% to form a light emitting layer having a thickness of 300 Pa by vacuum deposition.
  • PhGD see the following formula
  • BAlq (Bis (2-methyl-8-quinolinolato-N1, O8)-(1,1'-Biphenyl-4-olato) aluminum] 50um and Alq3 [Tris (8-hydroxyquinolinato) aluminium] 250 ⁇ Laminated sequentially to form an electron transport layer.
  • An organic light emitting device was manufactured by sequentially depositing LiF 5 ′ and Al 1000 ′ on the electron transport layer to form a cathode.
  • An organic light emitting diode was manufactured according to the same method as Example 7, except for using Examples 2 to 6 instead of Example 1 (A-6).
  • Example 7 an organic light emitting diode was manufactured according to the same method as Example 1 (A-6) 'except that Compound R1 was used as a host.
  • the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2) above.
  • Table 1 summarizes the device evaluation results.
  • Example 1 Classification Host Initial voltage (Vd) Current efficiency (cd / A) Power efficiency (lm / W) Luminance (cd / m 2 ) Color coordinates (CIEx) Color coordinates (CIEy) Comparative Example 1 R1 6.90 49.53 23.07 3000 0.333 0.623 Example 7 A-6 3.79 53.6 44.4 3000 0.358 0.615 Example 8 A-9 3.93 56.8 45.5 3000 0.366 0.609 Example 9 B-18 3.84 55.6 45.6 3000 0.346 0.618 Example 10 B-45 4.01 57.8 45.3 3000 0.357 0.611 Example 11 C-24 4.07 59.0 45.6 3000 0.356 0.615 Example 12 C-36 4.07 59.6 46.0 3000 0.368 0.607

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WO2013191177A1 (fr) * 2012-06-18 2013-12-27 東ソー株式会社 Composé azine cyclique, son procédé de fabrication, et élément électroluminescent organique le contenant
JP2015006995A (ja) * 2012-06-18 2015-01-15 東ソー株式会社 環状アジン化合物、その製造方法、及びそれを含有する有機電界発光素子
EP3015465A4 (fr) * 2013-07-29 2016-11-23 Lg Chemical Ltd Composé hétérocyclique et dispositif électroluminescent organique comprenant ledit composé
EP3184522A1 (fr) * 2015-12-22 2017-06-28 Samsung Electronics Co., Ltd. Composé cyclique condensé, dispositif électroluminescent organique comprenant le composé cyclique condensé, et procédé de fabrication du dispositif électroluminescent organique
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
EP3290411A1 (fr) * 2016-08-29 2018-03-07 Cynora Gmbh Molecules organiques, en particulier pour appareils organiques optoelectriques
WO2018145995A3 (fr) * 2017-02-07 2018-11-29 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques organiques
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WO2020099259A1 (fr) * 2018-11-16 2020-05-22 Cynora Gmbh Dérivés de carbazole destinés à être utilisés dans des dispositifs optoélectroniques
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CN111808076A (zh) * 2019-04-12 2020-10-23 冠能光电材料(深圳)有限责任公司 一种电子传输空穴阻挡有机材料及其在薄膜发光二极管应用
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WO2020101439A1 (fr) * 2018-11-16 2020-05-22 주식회사 엘지화학 Nouveau composé et diode électroluminescente organique le comprenant
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US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
JP2015006995A (ja) * 2012-06-18 2015-01-15 東ソー株式会社 環状アジン化合物、その製造方法、及びそれを含有する有機電界発光素子
WO2013191177A1 (fr) * 2012-06-18 2013-12-27 東ソー株式会社 Composé azine cyclique, son procédé de fabrication, et élément électroluminescent organique le contenant
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US10991892B2 (en) 2012-07-23 2021-04-27 Merck Patent Gmbh Materials for organic electroluminescent devices
EP3015465A4 (fr) * 2013-07-29 2016-11-23 Lg Chemical Ltd Composé hétérocyclique et dispositif électroluminescent organique comprenant ledit composé
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US11111231B2 (en) 2013-07-29 2021-09-07 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting device comprising same
US10217954B2 (en) 2013-11-13 2019-02-26 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
US10784446B2 (en) 2014-11-28 2020-09-22 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence element material, organic electroluminescence element and electronic device
EP3184522A1 (fr) * 2015-12-22 2017-06-28 Samsung Electronics Co., Ltd. Composé cyclique condensé, dispositif électroluminescent organique comprenant le composé cyclique condensé, et procédé de fabrication du dispositif électroluminescent organique
US10597403B2 (en) 2015-12-22 2020-03-24 Samsung Electronics Co., Ltd. Condensed cyclic compound, composition including the condensed cyclic compound, organic light-emitting device including the condensed cyclic compound, and method of manufacturing the organic light-emitting device
EP3290411A1 (fr) * 2016-08-29 2018-03-07 Cynora Gmbh Molecules organiques, en particulier pour appareils organiques optoelectriques
CN110249031A (zh) * 2017-02-07 2019-09-17 辛诺拉有限公司 特别用于有机光电器件的有机分子
US11456426B2 (en) 2017-02-07 2022-09-27 Samsung Display Co., Ltd. Organic molecules for use in organic optoelectronic devices
CN110249031B (zh) * 2017-02-07 2023-12-05 三星显示有限公司 特别用于有机光电器件的有机分子
WO2018145995A3 (fr) * 2017-02-07 2018-11-29 Cynora Gmbh Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques organiques
WO2020099259A1 (fr) * 2018-11-16 2020-05-22 Cynora Gmbh Dérivés de carbazole destinés à être utilisés dans des dispositifs optoélectroniques
CN113015727A (zh) * 2018-11-16 2021-06-22 辛诺拉有限公司 用于光电器件的咔唑衍生物
US11795161B2 (en) 2018-11-16 2023-10-24 Lg Chem, Ltd. Compound and organic light emitting device comprising same
CN111808076A (zh) * 2019-04-12 2020-10-23 冠能光电材料(深圳)有限责任公司 一种电子传输空穴阻挡有机材料及其在薄膜发光二极管应用

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